5-Amino-2-methylphenol → 8-(3-Hydroxy-4-methyl-phenylamino)imidazo[4,5-g]quinoline-7-carbonitrile

HRID 2213740Notes

Reaction equation

HRID 2213740 reaction equation
Cl[C:2]1[C:11]2[CH:10]=[C:9]3[N:12]=[CH:13][N:14]=[C:8]3[CH2:7][C:6]=2[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[NH2:17][C:18]1[CH:23]=[C:22]([OH:24])[C:21]([CH3:25])=[CH:20][CH:19]=1.Cl.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(OCCO)C>[OH:24][C:22]1[CH:23]=[C:18]([NH:17][C:2]2[C:11]3[CH:10]=[C:9]4[N:12]=[CH:13][N:14]=[C:8]4[CH2:7][C:6]=3[N:5]=[CH:4][C:3]=2[C:15]#[N:16])[CH:19]=[CH:20][C:21]=1[CH3:25]

Participants

6

Reactant 4

HCID 178185-Amino-2-methylphenolHCID 516892Sodium BicarbonateHCID 10176127Pyridinium chlorideHCID 693728438-Chloroimidazo[4,5-g]quinoline-7-carbonitrile

Product 1

HCID 693742998-(3-Hydroxy-4-methyl-phenylamino)imidazo[4,5-g]quinoline-7-carbonitrileYield 81.7%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A mixture of 0.15 g (0.66 mmol) of 8-chloroimidazo[4,5-g]quinoline-7-carbonitrile, 0.1 g (0.78 mmol) of 5-amino-o-cresol and 0.075 g (0.66 mmol) of pyridine hydrochloride in 5.0 mL of 2-ethoxyethanol is heated at reflux temperature for 1 hour, cooled to room temperature, poured into a saturated solution of sodium bicarbonate and stirred for 0.5 hour. The solid is collected by filtration, washed with water, diethyl ether, methylene chloride, tetrahydrofuran and dried in vacuo to yield 0.17 g of 8-(3-hydroxy-4-methyl-phenylamino)imidazo[4,5-g]quinoline-7-carbonitrile as white solid, mp 257–260° C. (dec).

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 1 hour
  3. filtrationThe solid is collected by filtration
  4. washwashed with water, diethyl ether, methylene chloride, tetrahydrofuran
  5. customdried in vacuo

Sources & evidence

ORD record
ord-fee4820cb81a4e8cb75854602ab478be
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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